Concept explainers
(a)
Interpretation: The structure of given compounds has to be drawn.
ethylacetoacetate
Concept introduction: The
Carboxylate ion with a carbonyl group at the 3-position loses
(a)
Answer to Problem 48P
The structure of ethyl acetoacetae is,
Explanation of Solution
The name given compound ethyl acetoacetate ends with ate. This means the given compound must contain an ester group. The name of compound starts with ethyl group, this means ethyl group is attached to the oxygen of an ester group. The acetone group is attached with the carbonyl carbon of an ester group. The structure of ethyl acetoacetae is,
(b)
Interpretation: The structure of given compounds has to be drawn.
α-methylmalonicacid
Concept introduction: The
Carboxylate ion with a carbonyl group at the 3-position loses
(b)
Answer to Problem 48P
The structure of α-methylmalonic acid is,
Explanation of Solution
The structure of malonic acid is two
(c)
Interpretation: The structure of given compounds has to be drawn.
β-keto ester
Concept introduction: The
Carboxylate ion with a carbonyl group at the 3-position loses
(c)
Answer to Problem 48P
The structure of β-keto ester is,
Explanation of Solution
The given compound β-keto ester contains a keto group and an ester group. The structure of β-keto ester is,
(d)
Interpretation: The structure of given compounds has to be drawn.
The carboxylic acid obtained from malonic ester synthesis when the
Concept introduction: The
Carboxylate ion with a carbonyl group at the 3-position loses
(d)
Answer to Problem 48P
The structure of enol form of cyclopentanone is,
Explanation of Solution
The compound cyclopentanone contain a keto group. After the keto enol tautomerism the keto compound converted into an alcohol and a double bond. The structure of enol form of cyclopentanone is,
(e)
Interpretation: The structure of given compounds has to be drawn.:
The structure of enol form of cyclopentanone
Concept introduction: The
Carboxylate ion with a carbonyl group at the 3-position loses
(e)
Answer to Problem 48P
The structure of the carboxylic acid obtained from malonic ester synthesis by using propyl bromide is,
Explanation of Solution
The proton removed from the alpha carbon of malonic ester by the base. Then, there is a nucleophilic substitution reaction takes place between the propyl bromide and carbanion of malonic ester. The third step is acidic hydrolysis of an ester to form carboxylic acid. The fourth step is decarboxylation of the compound to form the desired product. The reaction and structure of given compound is,
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Chapter 17 Solutions
Organic Chemistry, Books a la Carte Edition (8th Edition)
- What is the final product when 5-nitrofuran-2-carbaldehyde is mixed with each of these: a) 4-bromophenylthydrazine hydrochloride b) 4-cyanophenylhydrazine hydrochloride c) aminoguanidine bicarbonate d) 4-chlorophenylhydrazine hydrochloridearrow_forwardWhy is it not advisable to use aqueous hydrochloric acid in a Grignard reaction of a ketone? A) The Grignard reagent will react with the acid and cannot react with the ketone. B) The ketone will be protonated and will become unreactive. C) The ketone will form an unreactive enol. D) The Grignard reagent won't dissolve in aqueous solutionsarrow_forwardCreate 3-methyl-1-butanamine using the four different methods below. a. Gabriel synthesis b. Using sodium azide c. Using a carboxylic acid d. Using an alkyl bromidearrow_forward
- Nabumetone is a pain reliever and anti-inflammatory agent sold under the brand name of Relafen. a. Write out a synthesis of nabumetone from ethyl acetoacetate. b. What ketone and alkyl halide are needed to synthesize nabumetone by direct enolate alkylation?arrow_forwardWhy is only one amide obtained from the reaction of acetyl chloride with an equivalent of ethylamineand an equivalent of triethylamine?arrow_forwardThe reaction of a nitrile with an alcohol in the presence of a strong acid forms an N-substituted amide. This reaction, known as the Ritter reaction, doesnot work with primary alcohols. a. Why does the Ritter reaction not work with primary alcohols? b. Provide an explanation for why an amide is less susceptible to nucleophilic attack than its corresponding ester.arrow_forward
- 4-methoxybenzoic acid is less or more polar than 4-methoxyacetophenone? explain why (WITHOUT DRAWINGS)arrow_forwardNabumetone is a pain reliever and anti-inammatory agent sold under the brand name of Relafen.a. Write out a synthesis of nabumetone from ethyl acetoacetate.b. What ketone and alkyl halide are needed to synthesize nabumetone by direct enolate alkylation?arrow_forwardWhat Grignard reagent and aldehyde (or ketone) are needed to prepare attached alcohol? Show all possible routes.arrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning